Sodium Azide → HCID 18538111, compound

HRID 2187996Notes

Reaction equation

HRID 2187996 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH:6]1[CH2:10][C:9](=[O:11])[CH:8]=[CH:7]1>CN(C)C=O.C(OCC)(=O)C>[N:1]([CH:6]1[CH2:10][C:9](=[O:11])[CH:8]=[CH:7]1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 111056584-bromocyclopent-2-en-1-one

Product 1

HCID 18538111HCID 18538111, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of sodium azide (2.12 g, 32.6 mmol) in dimethylformamide (15 mL) cooled to 0° C. was added dropwise with stirring 4-bromocyclopent-2-enone (DePuy, C. H.; Isaks, M.; Eilers, K. L.; Morris, G. F. J. Org. Chem. 1964. 29, 3503; 3.5 g, 21.7 mmol) in dimethyl-formamide (5 mL) over a period of 5 min. The reaction mixture was stirred at 0° C. for 30 min and diluted with ethyl acetate (20 mL). The reaction mixture was washed with water (2×20 mL) and brine (20 mL), dried (MgSO4), filtered, and concentrated in vacuo to furnish an oily residue. Purification of the crude oil by flash column chromatography (10-15% ethyl acetate in hexane) gave 1.9 g (71%) of 4-azidocyclopent-2-enone as a light-yellow oil.

Workup

  1. washThe reaction mixture was washed with water (2×20 mL) and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto furnish an oily residue
  6. customPurification of the crude oil by flash column chromatography (10-15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c4a182257cef44f89de181ce8f4b374f
Source dataset
uspto-grants-2002_06
Patent number
US06410594B1

Reaction notes

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